NO855244L - Fremgangsmaate for fremstilling av fosforholdige organiske forbindelser. - Google Patents
Fremgangsmaate for fremstilling av fosforholdige organiske forbindelser.Info
- Publication number
- NO855244L NO855244L NO855244A NO855244A NO855244L NO 855244 L NO855244 L NO 855244L NO 855244 A NO855244 A NO 855244A NO 855244 A NO855244 A NO 855244A NO 855244 L NO855244 L NO 855244L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- radical
- general formula
- carbon atoms
- stated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- -1 PHOSPHORUS ORGANIC COMPOUNDS Chemical class 0.000 title description 14
- 229910052698 phosphorus Inorganic materials 0.000 title description 2
- 239000011574 phosphorus Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical group 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 27
- OJTRKMSUJCHVMW-UHFFFAOYSA-N 2-chloro-n-methyl-n-methylsulfonylacetamide Chemical compound CS(=O)(=O)N(C)C(=O)CCl OJTRKMSUJCHVMW-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- LEWADWGCENKZJX-UHFFFAOYSA-N n-(diethoxyphosphorylmethyl)-1-phenylmethanamine Chemical compound CCOP(=O)(OCC)CNCC1=CC=CC=C1 LEWADWGCENKZJX-UHFFFAOYSA-N 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- SAEILGZODTXRSQ-UHFFFAOYSA-N N-[di(propan-2-yloxy)phosphorylmethyl]-1-phenylmethanamine Chemical compound C(C1=CC=CC=C1)NCP(OC(C)C)(=O)OC(C)C SAEILGZODTXRSQ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- SSRTWWHQKYWDLC-UHFFFAOYSA-N N-(dimethoxyphosphorylmethyl)-1-phenylmethanamine Chemical compound COP(=O)(OC)CNCC1=CC=CC=C1 SSRTWWHQKYWDLC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- URAZVWXGWMBUGJ-UHFFFAOYSA-N di(propan-2-yl)azanium;chloride Chemical compound [Cl-].CC(C)[NH2+]C(C)C URAZVWXGWMBUGJ-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60Q—ARRANGEMENT OF SIGNALLING OR LIGHTING DEVICES, THE MOUNTING OR SUPPORTING THEREOF OR CIRCUITS THEREFOR, FOR VEHICLES IN GENERAL
- B60Q1/00—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor
- B60Q1/0064—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor with provision for maintenance, e.g. changing the light bulb
- B60Q1/007—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor with provision for maintenance, e.g. changing the light bulb via a removable cap
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
- F21S41/00—Illuminating devices specially adapted for vehicle exteriors, e.g. headlamps
- F21S41/10—Illuminating devices specially adapted for vehicle exteriors, e.g. headlamps characterised by the light source
- F21S41/19—Attachment of light sources or lamp holders
- F21S41/196—Wire spring attachments
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
- F21S41/00—Illuminating devices specially adapted for vehicle exteriors, e.g. headlamps
- F21S41/10—Illuminating devices specially adapted for vehicle exteriors, e.g. headlamps characterised by the light source
- F21S41/19—Attachment of light sources or lamp holders
- F21S41/198—Snap-fit attachments
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
- F21S41/00—Illuminating devices specially adapted for vehicle exteriors, e.g. headlamps
- F21S41/50—Illuminating devices specially adapted for vehicle exteriors, e.g. headlamps characterised by aesthetic components not otherwise provided for, e.g. decorative trim, partition walls or covers
- F21S41/55—Attachment thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Mechanical Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Fertilizers (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8420151A FR2575161B1 (fr) | 1984-12-26 | 1984-12-26 | Preparation d'intermediaires phosphores pour usages herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO855244L true NO855244L (no) | 1986-06-27 |
Family
ID=9311173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO855244A NO855244L (no) | 1984-12-26 | 1985-12-23 | Fremgangsmaate for fremstilling av fosforholdige organiske forbindelser. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0189725B1 (de) |
| JP (1) | JPS61158991A (de) |
| KR (1) | KR930007996B1 (de) |
| CN (1) | CN85109729A (de) |
| AT (1) | ATE41153T1 (de) |
| AU (1) | AU573410B2 (de) |
| BR (1) | BR8506478A (de) |
| CA (1) | CA1244461A (de) |
| DD (1) | DD251135A5 (de) |
| DE (1) | DE3568579D1 (de) |
| DK (1) | DK603585A (de) |
| ES (1) | ES8706161A1 (de) |
| FI (1) | FI855066A (de) |
| FR (1) | FR2575161B1 (de) |
| HU (1) | HU199855B (de) |
| IL (1) | IL77445A (de) |
| NO (1) | NO855244L (de) |
| PT (1) | PT81756B (de) |
| ZA (1) | ZA859769B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES534413A0 (es) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | Procedimiento de preparacion de sulfonamidas con grupo ansinometilfosfonico |
| FR2576024B1 (fr) * | 1985-01-14 | 1988-01-08 | Rhone Poulenc Agrochimie | Herbicides de type n - (phosphonomethylglycyl) sulfonylamines |
| FR2579210B1 (fr) * | 1985-03-21 | 1987-09-11 | Rhone Poulenc Agrochimie | Preparation d'herbicides a groupe phosphonates et d'intermediaires a partir de benzoxazines |
| FR2608609B1 (fr) * | 1986-12-18 | 1989-06-02 | Rhone Poulenc Agrochimie | Preparation d'intermediaires phosphores pour usage herbicide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414158A (en) * | 1980-04-29 | 1983-11-08 | Ciba-Geigy Corporation | Phosphonomethylglycylhydroxamic acid and novel herbicidally active salts thereof |
-
1984
- 1984-12-26 FR FR8420151A patent/FR2575161B1/fr not_active Expired
-
1985
- 1985-12-18 FI FI855066A patent/FI855066A/fi not_active Application Discontinuation
- 1985-12-20 CA CA000498283A patent/CA1244461A/en not_active Expired
- 1985-12-20 AU AU51519/85A patent/AU573410B2/en not_active Ceased
- 1985-12-20 ZA ZA859769A patent/ZA859769B/xx unknown
- 1985-12-23 HU HU854956A patent/HU199855B/hu unknown
- 1985-12-23 DD DD85285097A patent/DD251135A5/de unknown
- 1985-12-23 PT PT81756A patent/PT81756B/pt not_active IP Right Cessation
- 1985-12-23 DK DK603585A patent/DK603585A/da not_active Application Discontinuation
- 1985-12-23 NO NO855244A patent/NO855244L/no unknown
- 1985-12-24 JP JP60291796A patent/JPS61158991A/ja active Pending
- 1985-12-24 BR BR8506478A patent/BR8506478A/pt unknown
- 1985-12-24 IL IL77445A patent/IL77445A/xx unknown
- 1985-12-24 DE DE8585420242T patent/DE3568579D1/de not_active Expired
- 1985-12-24 EP EP85420242A patent/EP0189725B1/de not_active Expired
- 1985-12-24 AT AT85420242T patent/ATE41153T1/de not_active IP Right Cessation
- 1985-12-25 CN CN198585109729A patent/CN85109729A/zh active Pending
- 1985-12-26 ES ES550424A patent/ES8706161A1/es not_active Expired
- 1985-12-26 KR KR1019850009835A patent/KR930007996B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| HUT39751A (en) | 1986-10-29 |
| ZA859769B (en) | 1986-09-24 |
| KR930007996B1 (ko) | 1993-08-25 |
| CN85109729A (zh) | 1986-07-09 |
| FR2575161B1 (fr) | 1989-03-31 |
| DK603585D0 (da) | 1985-12-23 |
| JPS61158991A (ja) | 1986-07-18 |
| PT81756A (fr) | 1986-01-02 |
| FI855066A (fi) | 1986-06-27 |
| EP0189725A1 (de) | 1986-08-06 |
| DE3568579D1 (en) | 1989-04-13 |
| AU5151985A (en) | 1986-07-03 |
| IL77445A (en) | 1989-09-10 |
| KR860004902A (ko) | 1986-07-16 |
| CA1244461A (en) | 1988-11-08 |
| FI855066A0 (fi) | 1985-12-18 |
| AU573410B2 (en) | 1988-06-09 |
| FR2575161A1 (fr) | 1986-06-27 |
| HU199855B (en) | 1990-03-28 |
| ES550424A0 (es) | 1987-06-01 |
| DK603585A (da) | 1986-06-27 |
| ES8706161A1 (es) | 1987-06-01 |
| DD251135A5 (de) | 1987-11-04 |
| ATE41153T1 (de) | 1989-03-15 |
| EP0189725B1 (de) | 1989-03-08 |
| BR8506478A (pt) | 1986-09-02 |
| PT81756B (pt) | 1988-04-21 |
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